By Dan Koday
Updated March 17, 2016
Credit: © Dan Koday/Yves Yakoubyan

Cuba has long been out of reach for the casual American traveler, and like most hard-to-get things (we're looking at you sex and the Cronut), it's all anyone seems to be talking about. If you don't have a friend that's already been to the island, you certainly have a friend who won't stop talking about going. Just yesterday, President Obama gave another boost to the Cuba curious when he further loosened restrictions on the already existing people-to-people travel for Americans visiting Cuba, in which the travelers, not third party companies connect to Cubans.

“The new rules mean that individuals can now come on their own to Cuba without relying on a travel agent or tour company to arrange and certify their programs,” says Collin Laverty, an American living and working in Cuba who runs Cuba Educational Travel. That means that Americans can plan their own travel itineraries as long as they plan to share experiences, and interact with Cuban people. And though sipping Cuba Libres at Margaritaville after a day at the beach is still not in the cards (yet), Laverty says educational travel, the favored category for Americans, can mean anything from “cooking classes, to salsa dancing, to cocktails with Cuban friends.” Basically, as long as you can show you were participating in Cuban culture, you’re good.

But while the loosened restrictions mean you can now technically cut them out, booking through a tour operator like Cuba Educational Travel is helpful as they can assist you in getting from point A to B and planning the cultural activities and experiences. Keep in mind access to Internet is extremely limited in Cuba, so saying eff it and jumping on Google Maps when you’re lost or pulling up Yelp when you're hungry is not really a possibility. Having a tour operator and their staff to handle logistics, and speak the language will be very valuable whether you plan an itinerary centered around food, music, dance, art, tobacco, or a combination of all those things.

How to Get There

Though many U.S. airlines are looking at and competing to operate nonstop flights to Cuba in the near future, your best bet is still to book through charter companies like Cuba Travel Services, which have been operating direct flights from New York, Los Angeles, Miami and Tampa for years. Make sure to plan in advance as seats fill up quickly. If all else fails, you can book on Kayak but in the absence of American commercial flights, it will come with a stopover in either Canada or Mexico, doubling or even tripling the amount of travel time.

Where to Crash

The phrase "mi casa es su casa" could not be more fitting for Cuba, where casa particulars or homestays have always been the norm. In the spirit of people-to-people travel, Airbnb is becoming a more effective option and according to the site, Havana is their fastest growing market. Some rentals come with live-in house managers (which translates to home-cooked meals and help with directions to the elusive “Wifi Parks”), and some offer a more authentic taste of Cuban life by letting you stay with an entire family.

And remember, Cuba does have some tourist infrastructure, although, it’s still a far cry from the American tourist industry. So while there are traditional hotels, like the elegant and historic Hotel Nacional—an old school favorite of Frank Sinatra and Dean Martin, many are the sorts of cold war-era institutions that could use some updating. But traditional hotels are a sure bet if you're looking to score an Internet connection. Ask the front desk attendant to purchase a Tarjeta de Navegacion, a government-issued card that gives you a username and password to get online in designated hotspots (you’ll know you’re in the right place if you see hoards of people crowding around a single spot).

Getting Around

Cubans invented the idea of ride sharing à la Uber Pool and Lyft Line way before the apps ever existed. In fact, many taxis in Havana run on designated routes like a bus or subway might and you split the cost with locals or other travelers. It’s relatively inexpensive at $3-5 per rider (depending on how far you’re going), but make sure to tell the driver where you’re going first...if it’s not on his route, he’ll politely point you to another nearby option. If you'd prefer to ride solo, that’s always a possibility for a little more cash; some drivers will even offer to be your personal chauffeur for a 24-hour period—prices between $25-60 depending on the vehicle.

What to Do

Each itinerary in Cuba will certainly be different and can be customized for your desires, but no trip will be complete without visiting Habana Vieja (Old Havana), where you should get lost in a walking tour of the four main squares — Plaza Vieja, Plaza de San Francisco, Plaza de la Catedral and Plaza de Armas. It may sound old school, but with the Internet issues, make sure you print out or purchase a map ($1.50) to get around.

In Havana, you shouldn’t miss a walk along Malecón — the seawall road that hugs the water where Cubans and tourists alike come to congregate.

Hemingway’s House (known as Finca Vigía) is just outside of town and worthy of exploring on a clear day when views of downtown Havana can be seen from the property’s tower.

If you have time in Havana, take in a performance of dance, theater or opera at the Gran Teatro de la Habana, an impressive theater that has recently been restored to its former glory. If you have even more time than that, consider an overnight trip to Vinales, the breathtaking valley region famous for its tobacco production and mogote hill landscapes, where you can visit the farms and partake in activities like horseback riding and cycling.

Where to Eat

But before you do gotta eat, right? Paladares are privately run restaurants that look and feel like any other eating establishment, but are technically found inside someone’s home.

Ask around for recommendations as some of the best paladares might be have nothing but a discretely marked door you’d otherwise miss.

Atelier, Havana; Calle 5ta., No. 511 altos, entre Paseo y 2

This beautiful paladar offers indoor and outdoor dining in a romantic setting that is perfect for dinner.

El Del Frente, Havana; 303 O'Reilly, Havana, Cuba

Open the door and walk up a steep staircase to find yourself in this bright and airy space, complete with a beautiful rooftop garden where you can hang out after your meal. Do not leave without trying the lobster risotto!

Buena Paga, Havana; Aguacate between Obrapia & Obispo in Habana Vieja

On the outside, this dive may look like the Cuban version of a Subway. Inside, they make all types of incredible pressed sandwiches, everything from a classic Cubano and medianoche to pan con chorizo.

El Cocinero, Havana; Calle 26 between Calle 11 & 13

Located near the trendy FAC (Fabrica de Arte Cubano) building where the hipster scene hangs at night, this restaurant — located in an old peanut oil factory — attracts a trendier Havana crowd to its lively rooftop.

Coppelia, Havana; Calle 23 & L

The line runs literally around the block for this famous ice cream palace. And while it may be the Magnolia Bakery of Havana, it’s certainly worth the wait.

Museo Del Chocolate, Havana; Calle Amargura in Old Havana

Crowds form (for good reason) for this chocolate shop located in Old Havana. Try the Fiesta de praline, Havana club anejo, Azahar and Trufa de Avellana —you will not be disappointed.

Finca Paraiso Agroecologica, Vinales; Carretera Al Cementerio KM 1 1/2

This agro-ecological farm gives farm-to-table a new definition since you’re literally eating on the farm. Full of rustic charm, the fantastic views of the valley are only rivaled by the food, which pours out of the kitchen one plate after the other. Come hungry!